#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/07/2210763.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210763
loop_
_publ_author_name
'Jun Wan'
'Zheng-Zhong Peng'
'Xue-Mei Li'
'Ping-Kai Ouyang'
'Shu-Sheng Zhang'
_publ_section_title
;
 2-(1H-1,2,3-Benzotriazol-1-ylmethyl)-1-(4-methylbenzoyl)ethyl
 benzoate
;
_journal_coeditor_code           RZ2065
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4410
_journal_page_last               o4411
_journal_paper_doi               10.1107/S160053680603649X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H19 N3 O3'
_chemical_formula_moiety         'C23 H19 N3 O3'
_chemical_formula_sum            'C23 H19 N3 O3'
_chemical_formula_weight         385.41
_chemical_name_systematic
;
2-(1H-1,2,3-Benzotriazol-1-ylmethyl)-1-(4-methylbenzoyl)ethyl benzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.4820(10)
_cell_angle_beta                 96.9280(10)
_cell_angle_gamma                97.4440(10)
_cell_formula_units_Z            2
_cell_length_a                   9.5987(9)
_cell_length_b                   10.2272(9)
_cell_length_c                   11.4321(10)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3
_cell_measurement_theta_min      2.2
_cell_volume                     975.72(15)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Siemens SMART 1000 CCD area-detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4423
_diffrn_reflns_theta_full        25.62
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0637P)²+0.235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                2400
_reflns_number_total             2808
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2065.cif
_cod_data_source_block           I
_cod_database_code               2210763
_cod_database_fobs_code          2210763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.35691(15) -0.19998(15) -0.10902(13) 0.0602(4) Uani d . 1
O O2 0.27471(13) 0.05300(13) 0.02400(12) 0.0487(3) Uani d . 1
O O3 0.08513(15) -0.11326(16) 0.00589(14) 0.0624(4) Uani d . 1
N N1 0.29377(16) 0.23075(16) -0.12395(14) 0.0463(4) Uani d . 1
N N2 0.1929(2) 0.2293(2) -0.21863(17) 0.0636(5) Uani d . 1
N N3 0.1584(2) 0.3603(2) -0.17273(19) 0.0715(5) Uani d . 1
C C1 0.2678(2) -0.4053(2) -0.3791(2) 0.0607(6) Uani d . 1
H H1A 0.3230 -0.4327 -0.3245 0.073 Uiso calc R 1
C C2 0.2219(2) -0.5040(2) -0.5132(2) 0.0687(6) Uani d . 1
H H2A 0.2468 -0.5971 -0.5473 0.082 Uiso calc R 1
C C3 0.1398(2) -0.4676(2) -0.59828(19) 0.0553(5) Uani d . 1
C C4 0.1037(2) -0.3298(2) -0.5439(2) 0.0617(6) Uani d . 1
H H4A 0.0478 -0.3030 -0.5986 0.074 Uiso calc R 1
C C5 0.1487(2) -0.2300(2) -0.40962(19) 0.0551(5) Uani d . 1
H H5A 0.1225 -0.1377 -0.3756 0.066 Uiso calc R 1
C C6 0.23259(19) -0.26602(19) -0.32503(17) 0.0429(4) Uani d . 1
C C7 0.28356(19) -0.1651(2) -0.18038(18) 0.0434(4) Uani d . 1
C C8 0.2472(2) -0.00956(19) -0.11868(16) 0.0434(4) Uani d . 1
H H8A 0.1466 -0.0155 -0.1527 0.052 Uiso calc R 1
C C9 0.3454(2) 0.0956(2) -0.14894(18) 0.0467(5) Uani d . 1
H H9A 0.4403 0.1220 -0.0944 0.056 Uiso calc R 1
H H9B 0.3536 0.0444 -0.2417 0.056 Uiso calc R 1
C C10 0.32478(19) 0.36633(19) -0.01334(18) 0.0431(4) Uani d . 1
C C11 0.2376(2) 0.4487(2) -0.0452(2) 0.0539(5) Uani d . 1
C C12 0.2421(3) 0.5976(2) 0.0466(3) 0.0700(6) Uani d . 1
H H12A 0.1842 0.6542 0.0269 0.084 Uiso calc R 1
C C13 0.3346(3) 0.6554(2) 0.1656(3) 0.0731(7) Uani d . 1
H H13A 0.3399 0.7537 0.2287 0.088 Uiso calc R 1
C C14 0.4221(3) 0.5706(2) 0.1955(2) 0.0679(6) Uani d . 1
H H14A 0.4842 0.6147 0.2781 0.081 Uiso calc R 1
C C15 0.4197(2) 0.4258(2) 0.10813(19) 0.0537(5) Uani d . 1
H H15A 0.4782 0.3701 0.1287 0.064 Uiso calc R 1
C C16 0.1889(2) -0.0166(2) 0.07369(19) 0.0452(5) Uani d . 1
C C17 0.2401(2) 0.03695(19) 0.21784(18) 0.0449(4) Uani d . 1
C C18 0.3727(2) 0.1293(2) 0.28646(19) 0.0563(5) Uani d . 1
H H18A 0.4305 0.1655 0.2433 0.068 Uiso calc R 1
C C19 0.4191(3) 0.1678(3) 0.4183(2) 0.0728(7) Uani d . 1
H H19A 0.5094 0.2278 0.4635 0.087 Uiso calc R 1
C C20 0.3328(3) 0.1180(3) 0.4833(2) 0.0782(7) Uani d . 1
H H20A 0.3645 0.1446 0.5727 0.094 Uiso calc R 1
C C21 0.2002(3) 0.0293(3) 0.4175(2) 0.0731(7) Uani d . 1
H H21A 0.1412 -0.0023 0.4628 0.088 Uiso calc R 1
C C22 0.1535(2) -0.0135(2) 0.2842(2) 0.0597(5) Uani d . 1
H H22A 0.0644 -0.0759 0.2391 0.072 Uiso calc R 1
C C23 0.0879(3) -0.5780(3) -0.7435(2) 0.0754(7) Uani d . 1
H H23A 0.0330 -0.5343 -0.7871 0.113 Uiso calc R 1
H H23B 0.0288 -0.6661 -0.7518 0.113 Uiso calc R 1
H H23C 0.1687 -0.6040 -0.7844 0.113 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C16 O2 C8 115.83(14) ?
N2 N1 C10 110.27(15) ?
N2 N1 C9 119.28(15) ?
C10 N1 C9 130.37(15) ?
N3 N2 N1 108.72(16) ?
N2 N3 C11 108.05(16) ?
C2 C1 C6 120.81(19) ?
C2 C1 H1A 119.6 ?
C6 C1 H1A 119.6 ?
C1 C2 C3 121.5(2) ?
C1 C2 H2A 119.3 ?
C3 C2 H2A 119.3 ?
C4 C3 C2 117.51(18) ?
C4 C3 C23 121.7(2) ?
C2 C3 C23 120.7(2) ?
C3 C4 C5 121.55(19) ?
C3 C4 H4A 119.2 ?
C5 C4 H4A 119.2 ?
C4 C5 C6 120.81(19) ?
C4 C5 H5A 119.6 ?
C6 C5 H5A 119.6 ?
C1 C6 C5 117.82(17) ?
C1 C6 C7 118.54(16) ?
C5 C6 C7 123.62(17) ?
O1 C7 C6 122.00(17) ?
O1 C7 C8 118.59(16) ?
C6 C7 C8 119.38(15) ?
O2 C8 C9 105.95(14) yes
O2 C8 C7 109.59(14) yes
C9 C8 C7 110.18(14) yes
O2 C8 H8A 110.3 ?
C9 C8 H8A 110.3 ?
C7 C8 H8A 110.3 ?
N1 C9 C8 112.55(15) ?
N1 C9 H9A 109.1 ?
C8 C9 H9A 109.1 ?
N1 C9 H9B 109.1 ?
C8 C9 H9B 109.1 ?
H9A C9 H9B 107.8 ?
N1 C10 C15 133.26(17) ?
N1 C10 C11 104.33(16) ?
C15 C10 C11 122.40(18) ?
N3 C11 C10 108.63(17) ?
N3 C11 C12 131.0(2) ?
C10 C11 C12 120.4(2) ?
C13 C12 C11 117.1(2) ?
C13 C12 H12A 121.4 ?
C11 C12 H12A 121.4 ?
C12 C13 C14 121.6(2) ?
C12 C13 H13A 119.2 ?
C14 C13 H13A 119.2 ?
C15 C14 C13 122.4(2) ?
C15 C14 H14A 118.8 ?
C13 C14 H14A 118.8 ?
C14 C15 C10 116.07(19) ?
C14 C15 H15A 122.0 ?
C10 C15 H15A 122.0 ?
O3 C16 O2 122.85(17) ?
O3 C16 C17 124.81(17) ?
O2 C16 C17 112.32(16) ?
C18 C17 C22 119.34(18) ?
C18 C17 C16 122.51(17) ?
C22 C17 C16 118.09(18) ?
C19 C18 C17 120.18(19) ?
C19 C18 H18A 119.9 ?
C17 C18 H18A 119.9 ?
C20 C19 C18 120.1(2) ?
C20 C19 H19A 119.9 ?
C18 C19 H19A 119.9 ?
C21 C20 C19 120.3(2) ?
C21 C20 H20A 119.8 ?
C19 C20 H20A 119.8 ?
C20 C21 C22 120.3(2) ?
C20 C21 H21A 119.9 ?
C22 C21 H21A 119.9 ?
C21 C22 C17 119.8(2) ?
C21 C22 H22A 120.1 ?
C17 C22 H22A 120.1 ?
C3 C23 H23A 109.5 ?
C3 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C3 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.214(2) yes
O2 C16 1.352(2) yes
O2 C8 1.436(2) yes
O3 C16 1.202(2) yes
N1 N2 1.356(2) ?
N1 C10 1.360(2) ?
N1 C9 1.448(2) ?
N2 N3 1.308(2) ?
N3 C11 1.378(3) ?
C1 C2 1.380(3) ?
C1 C6 1.384(3) ?
C1 H1A 0.9300 ?
C2 C3 1.386(3) ?
C2 H2A 0.9300 ?
C3 C4 1.374(3) ?
C3 C23 1.504(3) ?
C4 C5 1.383(3) ?
C4 H4A 0.9300 ?
C5 C6 1.387(3) ?
C5 H5A 0.9300 ?
C6 C7 1.480(2) ?
C7 C8 1.534(2) yes
C8 C9 1.521(2) yes
C8 H8A 0.9800 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C15 1.388(3) ?
C10 C11 1.388(3) ?
C11 C12 1.403(3) ?
C12 C13 1.357(3) ?
C12 H12A 0.9300 ?
C13 C14 1.399(3) ?
C13 H13A 0.9300 ?
C14 C15 1.363(3) ?
C14 H14A 0.9300 ?
C15 H15A 0.9300 ?
C16 C17 1.479(3) ?
C17 C18 1.384(3) ?
C17 C22 1.387(3) ?
C18 C19 1.375(3) ?
C18 H18A 0.9300 ?
C19 C20 1.370(3) ?
C19 H19A 0.9300 ?
C20 C21 1.368(3) ?
C20 H20A 0.9300 ?
C21 C22 1.380(3) ?
C21 H21A 0.9300 ?
C22 H22A 0.9300 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C23 H23C Cg 1_544 0.96 2.85 3.572 133 yes
C9 H9A O1 2_655 0.97 2.59 3.517(2) 161 yes
C15 H15A O1 2_655 0.93 2.46 3.351(3) 161 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C10 N1 N2 N3 0.3(2)
C9 N1 N2 N3 177.37(16)
N1 N2 N3 C11 -0.4(2)
C6 C1 C2 C3 0.2(4)
C1 C2 C3 C4 -0.8(3)
C1 C2 C3 C23 -178.6(2)
C2 C3 C4 C5 0.7(3)
C23 C3 C4 C5 178.4(2)
C3 C4 C5 C6 0.1(3)
C2 C1 C6 C5 0.7(3)
C2 C1 C6 C7 179.48(19)
C4 C5 C6 C1 -0.8(3)
C4 C5 C6 C7 -179.57(18)
C1 C6 C7 O1 1.3(3)
C5 C6 C7 O1 -179.98(19)
C1 C6 C7 C8 179.31(17)
C5 C6 C7 C8 -2.0(3)
C16 O2 C8 C9 174.41(14)
C16 O2 C8 C7 -66.74(18)
O1 C7 C8 O2 -16.3(2)
C6 C7 C8 O2 165.61(15)
O1 C7 C8 C9 99.91(19)
C6 C7 C8 C9 -78.2(2)
N2 N1 C9 C8 -83.0(2)
C10 N1 C9 C8 93.4(2)
O2 C8 C9 N1 -76.41(17)
C7 C8 C9 N1 165.12(14)
N2 N1 C10 C15 -178.8(2)
C9 N1 C10 C15 4.6(3)
N2 N1 C10 C11 -0.1(2)
C9 N1 C10 C11 -176.75(17)
N2 N3 C11 C10 0.3(2)
N2 N3 C11 C12 179.4(2)
N1 C10 C11 N3 -0.1(2)
C15 C10 C11 N3 178.79(18)
N1 C10 C11 C12 -179.29(18)
C15 C10 C11 C12 -0.4(3)
N3 C11 C12 C13 -178.8(2)
C10 C11 C12 C13 0.2(3)
C11 C12 C13 C14 0.2(3)
C12 C13 C14 C15 -0.2(4)
C13 C14 C15 C10 0.0(3)
N1 C10 C15 C14 178.84(19)
C11 C10 C15 C14 0.3(3)
C8 O2 C16 O3 -8.7(2)
C8 O2 C16 C17 169.76(13)
O3 C16 C17 C18 168.57(19)
O2 C16 C17 C18 -9.8(2)
O3 C16 C17 C22 -8.5(3)
O2 C16 C17 C22 173.10(16)
C22 C17 C18 C19 1.4(3)
C16 C17 C18 C19 -175.62(19)
C17 C18 C19 C20 -1.7(4)
C18 C19 C20 C21 0.3(4)
C19 C20 C21 C22 1.4(4)
C20 C21 C22 C17 -1.7(4)
C18 C17 C22 C21 0.2(3)
C16 C17 C22 C21 177.43(18)
